Greatest head-to-heads in jumps racing, from Arkle v Mill House to Denman v Kauto Star and Shishkin v Energumene

Arkle v Mill House, Cheltenham Gold Cup, 1964

The epic battle between Shishkin and Energumene at Ascot over the weekend evokes memories of the best head-to-heads that jumps racing has had to offer and it’s a rivalry that bears a resemblance to the historic mid-1960s smash up between Arkle and Mill House.

Two virtually unbeaten chasers, one trained in Ireland, one trained in England. All of those ingredients are there again with the one exception being the 1964 Gold Cup was a rematch as Arkle and Mill House had already met.

Fulke Walwyn’s Mill House had beaten Arkle in that season’s Hennessy at Newbury, the 15/8 favourite giving 5lb and a beating to Tom Dreaper’s horse who slipped a couple of fences from home before finishing third.

That meant Mill House was sent off 8/13 in his quest for back-to-back Gold Cups, but with the pair clear of the rest it was Arkle (7/4) who proved the strongest up the famous hill, galloping his way to a five-length victory, then two more Gold Cups, some monstrous victories in handicaps, a record Timeform rating of 212 and racing immortality.

Monksfield v Sea Pigeon, Champion Hurdle, 1979

The 1970s and early 80s is considered a golden era for two-mile hurdlers and the roll of honour for the Champion Hurdle from 1976 to 1981 is a good synopsis of the story; two for Night Nurse, two for Monksfield and two for Sea Pigeon.

Des McDonagh’s Monksfield was something of a Cheltenham Festival legend and having finished second in the 1976 Triumph Hurdle he finished in the same position in the following year’s Champion Hurdle, defending champion Night Nurse seeing him off with Sea Pigeon in behind.

A year later in 1978 Monksfield gained his revenge, beating Sea Pigeon two lengths with Night Nurse five lengths further back in third, and with Peter Easterby sending the latter down the chasing route after that it was left to his stablemate to focus on Champion Hurdle glory.

Sea Pigeon eventually won two titles in 1980 and 81, but not before he’d cruised up looking the likely winner in 1979 - only for the grizzled Festival specialist Monksfield to fight back tenaciously under Dessie Hughes in an epic encounter and one that was symbolic of that golden era.

Desert Orchid v Panto Prince, Victor Chandler Chase, 1989

With a bloated graded-race schedule the Quality Jump Racing Review Group have promised to shake up the jumps Pattern and refine the programme which could lead to more good horses being forced into handicaps.

After all, their fifth aim is ‘to produce a race programme that is consistently more engaging to punters, fans, the media and racegoers’ and all four of those sections go misty-eyed at the feats of Arkle and Desert Orchid who never had a soft option and did extraordinary things in handicaps.

Of course, there’s a certain irony about harking back to the days of the old Victor Chandler Chase being a handicap in an article inspired by the modern incarnation of the same race throwing up Shishkin versus Energumene.

But Desert Orchid v Panto Prince on that sunny January day at Ascot in 1989 was something else. Dessie gave 22lb to his game, front-running, rival, but in a tremendous finish amongst a cacophony of crowd roar the people’s champion got up by a head thanks to a late thrust under Simon Sherwood in a mid-season classic.

Viking Flagship v Deep Sensation, Melling Chase, 1995

Viking Flagship and Deep Sensation met seven times in 1994-1995 but you could hardly call it a rivalry, with David Nicholson’s dual Champion Chase hero coming out on top on each and every occasion.

The two-year older Deep Sensation had won the Champion Chase himself for Josh Gifford in 1993, but he retained his ability and in-between some of his Viking Flagship defeats he won handicap chases at Ascot and Cheltenham off marks in the 160s.

A five-length second to his old nemesis in the 1995 Champion Chase when ridden by Norman Williamson for the first time, the pair reunited at Aintree just over three weeks’ later in a blockbuster of a Melling Chase.

In a thrilling climax the trio of Martha’s Son, Viking Flagship and Deep Sensation flew over the last in unison, with the latter finally looking like he’d get the better of Nicholson’s horse as he went ahead on the far rail.

But when you’ve got a rival’s number like Viking Flagship had Deep Sensation’s it ain’t over ‘til it’s over, and Adrian Maguire inspired a late charge out of his mount to get him up by a short head in the most dramatic of photo finishes.

Edredon Bleu v Direct Route, Queen Mother Champion Chase, 2000

Edredon Bleu, Direct Route and Flagship Uberalles had some memorable battles in the two-mile chase division at the turn of the century and none more so than at the Cheltenham Festival in 2000.

Paul Nicholls’ Flagship Uberalles was the up-and-coming novice the previous season and he beat Direct Route and Edredon Bleu in both the Haldon Gold Cup and Tingle Creek as he made a seamless transition to open company, while the former was behind him in the Victor Chandler, as well.

No wonder he was sent off the 11/10 favourite for the Queen Mother Champion Chase, but a mistake two from home eventually knocked the stuffing out of him and though the three were in a line at the last, it turned into a slug-fest up the hill between long-time leader Edredon Bleu and the rallying Direct Route.

Direct Route got at least a neck up on Edredon Bleu in the run for the line, but AP McCoy was not to be denied on the Henrietta Knight-trained horse, in the future Gold Cup-winning colours of owner Jim Lewis’ Best Mate, the pair edging it by a short head in a Festival barnstormer.

Hardy Eustace v Harchibald, Champion Hurdle, 2005

The best head-to-heads have a myriad of factors at play to help spice up the occasion and it’s hard to think of a better example of drama being played out thanks to the contrasting styles of the main protagonists than Hardy Eustace v Harchibald.

Hardy Eustace was the reigning champion, a two-time Festival winner, full of grit and determination, a game front-runner, blinkers back on to maximise his chance. Harchibald was all speed and flair and, having progressed through handicaps, now looked the real deal on the back of coming-of-age wins in the Fighting Fifth and Christmas Hurdles.

Brave Inca was the third stooge in this tale, but despite being a year older than Harchibald he was still on his ascent to the top, the best still to come from him when he won the following year’s Champion Hurdle.

Even though he was only beaten a neck and a neck, he never really seemed in this as the eye was drawn to Paul Carberry, motionless, cruising on Harchibald with Hardy Eustace in top gear.

We all know how it plays out, the mercurial stalker finding nothing when finally asked for his effort in the last 50 yards, his rider booed in amid furore, although subsequent events went on to prove he was the ultimate bridle horse. But while Hardy Eustace had a second Champion Hurdle in his satchel, who says you never remember who comes second.

Denman v Kauto Star, Cheltenham Gold Cup, 2008

As head-to-heads go, they don’t come any bigger than Ditcheat stablemates Denman v Kauto Star. By 2010 the rivalry had grown so big there were battle buses and rosettes involved for each ahead of the Cheltenham Gold Cup, only for the horse without fanfare, Imperial Commander, to spoil the party.

Like Hardy Eustace and Harchibald, these two had contrasting styles but both were a million miles away from being a bridle horse. Denman gained his ‘The Tank’ nickname thanks to his relentless galloping while Kauto Star had the sort of class rarely seen in a jumps horse as he danced his way to two Cheltenham Gold Cups and five King Georges.

The head-to-heads ended 3-1 in Denman’s favour but on the four occasions they met – each time in the Cheltenham Gold Cup – there was one victory for the stablemates apiece, the most thrilling coming when they were both in their pomp on March 14, 2008.

Denman, eight from eight over fences but sent off 9/4 second favourite given the size of his task against his awesome stablemate, put in a tremendous effort during an epic performance, Sam Thomas’ several over-the-shoulder looks to see where Kauto was in the closing stages just one of the memorable aspects of this most iconic and historic renewal of the Cheltenham Gold Cup.

Shishkin v Energumene, SBK Clarence House Chase, 2022

As the shiny Longines clock in the Ascot parade ring ticked 3.36pm everyone in racing held their breath at the prospect of a possible race for the ages. We got exactly that.

This was shiver down the spine stuff, whether you had a financial interest in the Clarence House Chase or not, as two steeplechasing heavyweights put their unbeaten records over fences on the line.

Four minutes and 16 seconds later only one of them had that unbeaten record intact, Shishkin, after an almighty race, one already comfortably sitting alongside the great head-to-heads jumps racing has delivered down the years; the likes of Arkle v Mill House, Desert Orchid v Panto Prince and Denman v Kauto Star.

For much of the contest the answer being Shishkin looked unlikely. He wasn’t faultless, he pecked on landing at one fence down the back, and he just looked to have been taken out of his comfort zone out wide as Paul Townend and Energumene ploughed along the rail relentlessly out in front.

At the top of the straight Townend sat quieter than Nico de Boinville. Shishkin traded at 7.8 in the run on Betfair. Energumene was travelling the better and Shishkin was being vigorously ridden along.

But crucially, despite all this, Energumene hadn’t put significant daylight between himself and Shishkin at this point. He rolled on out in front and a super leap at the last would’ve sealed it against most horses, but Shishkin isn’t most horses.

He found more, a power-packed finish, one reminiscent of Altior – that previous two-mile chasing great from Seven Barrows. Sprinter Sacre, Altior, Shishkin – Nicky Henderson has found another one, alright.

To come from two lengths down to beat a high-class horse like Energumene by half that margin was something special.

It didn’t only light up a gloomy Ascot Saturday, it lit up the season, the roar from a raucous reception prompting De Boinville – Gold Cup and Sprinter Sacre Champion Chase comeback-winning jockey De Boinville – to declare it the best he’s ever had on a racecourse.

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